EP4396305A4 - SYNTHESIS OF MDMA OR ITS OPTICALLY ACTIVE (R)- OR (S)-MDMA ISOMERS - Google Patents
SYNTHESIS OF MDMA OR ITS OPTICALLY ACTIVE (R)- OR (S)-MDMA ISOMERSInfo
- Publication number
- EP4396305A4 EP4396305A4 EP22865560.1A EP22865560A EP4396305A4 EP 4396305 A4 EP4396305 A4 EP 4396305A4 EP 22865560 A EP22865560 A EP 22865560A EP 4396305 A4 EP4396305 A4 EP 4396305A4
- Authority
- EP
- European Patent Office
- Prior art keywords
- mdma
- isomers
- synthesis
- optically active
- optically
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202163239853P | 2021-09-01 | 2021-09-01 | |
| PCT/US2022/042353 WO2023034510A1 (en) | 2021-09-01 | 2022-09-01 | Synthesis of mdma or its optically active ( r)- or ( s)-mdma isomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP4396305A1 EP4396305A1 (en) | 2024-07-10 |
| EP4396305A4 true EP4396305A4 (en) | 2025-08-27 |
Family
ID=85411549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP22865560.1A Pending EP4396305A4 (en) | 2021-09-01 | 2022-09-01 | SYNTHESIS OF MDMA OR ITS OPTICALLY ACTIVE (R)- OR (S)-MDMA ISOMERS |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11993577B2 (en) |
| EP (1) | EP4396305A4 (en) |
| CA (1) | CA3230380A1 (en) |
| MX (1) | MX2024002291A (en) |
| WO (1) | WO2023034510A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4396305A4 (en) | 2021-09-01 | 2025-08-27 | Empathbio Inc | SYNTHESIS OF MDMA OR ITS OPTICALLY ACTIVE (R)- OR (S)-MDMA ISOMERS |
| US12492178B2 (en) | 2021-09-01 | 2025-12-09 | Empathbio, Inc. | Stable polymorph of R-MDMA HCl |
| US11845736B2 (en) | 2021-10-01 | 2023-12-19 | Empathbio, Inc. | Prodrugs of MDMA, MDA, and derivatives thereof |
| EP4457222A4 (en) | 2021-12-28 | 2025-12-24 | Empathbio Inc | Nitrogen oxide-releasing prodrugs of MDA and MDMA |
| US20240217944A1 (en) * | 2022-12-31 | 2024-07-04 | ATAI Therapeutics AG | Salt forms of r-mdma and methods using the same |
Family Cites Families (48)
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|---|---|---|---|---|
| US3907864A (en) | 1973-02-15 | 1975-09-23 | Abbott Lab | Amino acid esters and amides of disubstituted phenethylamines |
| US4017636A (en) | 1973-10-23 | 1977-04-12 | Abbott Laboratories | Esters of γ-glutamyl amide of dopamine |
| JPH02124884A (en) | 1988-07-08 | 1990-05-14 | Zhongguo Yixuekexueyuan Yaowo Yanjiusuo | N-substituted amide derivative |
| US5061727A (en) | 1990-05-04 | 1991-10-29 | American Cyanamid Company | Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles |
| EP0888329A1 (en) | 1996-03-22 | 1999-01-07 | Du Pont Pharmaceuticals Company | NOVEL ASYMMETRIC SYNTHESIS OF R-$g(a)-PROPYL-PIPERONYL AMINE AND ITS ANALOGS |
| US6846492B2 (en) | 2000-02-23 | 2005-01-25 | Ciba Specialty Chemicals Corporation | Use of phenylethylamine derivatives for the antimicrobial treatment of surfaces |
| US6927036B2 (en) | 2002-02-19 | 2005-08-09 | Xero Port, Inc. | Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof |
| WO2005038049A2 (en) | 2003-10-06 | 2005-04-28 | Heinrich Guenther | System and method for optimizing drug therapy |
| US6991911B2 (en) | 2003-12-15 | 2006-01-31 | Dade Behring Inc. | Assay for entactogens |
| SG169238A1 (en) | 2004-08-11 | 2011-03-30 | Williamsburg Holdings Llc | Noncardiotoxic pharmaceutical compounds |
| GB0428232D0 (en) | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Compounds |
| US7642355B2 (en) | 2005-03-10 | 2010-01-05 | Theravance, Inc. | Biphenyl compounds useful as muscarinic receptor antagonists |
| JP2008537931A (en) | 2005-03-10 | 2008-10-02 | セラヴァンス， インコーポレーテッド | Biphenyl compounds useful as muscarinic receptor antagonists |
| US8877802B2 (en) | 2005-07-28 | 2014-11-04 | Duke Univerity | Antiparkinsonian action of phenylisopropylamines |
| WO2007090733A1 (en) | 2006-02-06 | 2007-08-16 | Nicox S.A. | Nitrooxy derivatives suitable as alpha2 adrenergic receptor agonists |
| WO2008016677A2 (en) | 2006-08-02 | 2008-02-07 | Auspex Pharmaceuticals, Inc. | Preparation and utility of deuterated amphetamines |
| WO2008033351A2 (en) | 2006-09-11 | 2008-03-20 | Theraquest Biosciences, Inc. | Multimodal abuse resistant and extended release formulations |
| US20080293695A1 (en) | 2007-05-22 | 2008-11-27 | David William Bristol | Salts of physiologically active and psychoactive alkaloids and amines simultaneously exhibiting bioavailability and abuse resistance |
| MX2009005509A (en) | 2006-12-07 | 2009-06-03 | Hoffmann La Roche | 2-aminoquinolines as 5-ht(5a) receptor antagonists. |
| US20090111741A1 (en) | 2007-10-10 | 2009-04-30 | Aldrich Jane V | Method for treating and/or preventing drug seeking behavior |
| RU2010136023A (en) | 2008-02-01 | 2012-03-10 | Асцендис Фарма Ас (Dk) | A MEDICINE CONTAINING A SELF-DIVISIBLE LINKER |
| CN101822841B (en) | 2010-04-12 | 2012-02-15 | 四川大学 | Application of organic amine derivatives as brain-targeting modification group of small-molecule drug |
| EA032840B8 (en) | 2011-06-22 | 2020-06-18 | Вайоми Терапеутикс Лимитед | Conjugate-based antifungal prodrugs and use thereof |
| EP2687854A1 (en) | 2012-07-19 | 2014-01-22 | Chiron AS | Test kit for the quantitative determination of narcotic drugs |
| US11123310B2 (en) | 2017-02-24 | 2021-09-21 | Pharmapotheca, Llc | Amphetamine controlled release, prodrug, and abuse-deterrent dosage forms |
| IL288554B2 (en) * | 2016-02-24 | 2024-02-01 | Chemapotheca LLC | Amphetamine controlled release, prodrug, and abuse deterrent dosage forms |
| TWI832295B (en) | 2018-10-11 | 2024-02-11 | 美商嘉來克生命科學有限責任公司 | Prodrug modulators of the integrated stress pathway |
| RU2732297C2 (en) | 2018-11-14 | 2020-09-15 | Общество с ограниченной ответственностью "Гурус БиоФарм" | Derivatives of non-steroid anti-inflammatory agents |
| AU2020228289A1 (en) | 2019-02-27 | 2021-09-09 | The Regents Of The University Of California | N-substituted indoles and other heterocycles for treating brain disorders |
| WO2020252384A1 (en) | 2019-06-14 | 2020-12-17 | Vorsanger Gary | Treatment methods utilizing oxytocin receptor agonists |
| US11660305B2 (en) | 2019-11-19 | 2023-05-30 | Turtle Bear Holdings, Llc | Tryptamine compositions for enhancing neurite outgrowth |
| CN120040398A (en) | 2020-06-08 | 2025-05-27 | 泰科根公司 | Advantageous benzofuran compositions for mental disorders or mental enhancement |
| CN116897043A (en) | 2020-07-01 | 2023-10-17 | 艾斯特希有限责任公司 | Polycyclic amines for opioid receptor modulation |
| CA3182412A1 (en) | 2020-07-06 | 2022-01-13 | Mathew BAGGOTT | Advantageous benzothiophene compositions for mental disorders or enhancement |
| CA3187217A1 (en) | 2020-08-06 | 2022-02-10 | Matthew BAGGOTT | 2-aminoindane compounds for mental disorders or enhancement |
| WO2022053696A1 (en) | 2020-09-11 | 2022-03-17 | Compass Pathfinder Limited | Novel safrylamine derivatives having prodrug properties |
| CA3192617A1 (en) | 2020-09-20 | 2022-03-24 | Matthew BAGGOTT | Advantageous tryptamine compositions for mental disorders or enhancement |
| JP2023549405A (en) | 2020-11-18 | 2023-11-24 | マインド メディシン， インコーポレイテッド | MDMA prodrugs to aid psychotherapy |
| CA3204457A1 (en) | 2021-01-06 | 2022-07-14 | Ben SESSA | Mdma in the treatment of alcohol use disorder |
| US20220267252A1 (en) | 2021-02-24 | 2022-08-25 | Mind Medicine, Inc. | Mescaline derivatives with modified action |
| WO2022235530A1 (en) | 2021-05-05 | 2022-11-10 | Mind Medicine, Inc. | Mdma enantiomers |
| WO2022256720A2 (en) | 2021-06-03 | 2022-12-08 | Arcadia Medicine, Inc. | Enantiomeric entactogen compositions and methods of their use |
| US12492178B2 (en) | 2021-09-01 | 2025-12-09 | Empathbio, Inc. | Stable polymorph of R-MDMA HCl |
| EP4396305A4 (en) | 2021-09-01 | 2025-08-27 | Empathbio Inc | SYNTHESIS OF MDMA OR ITS OPTICALLY ACTIVE (R)- OR (S)-MDMA ISOMERS |
| WO2023044027A1 (en) | 2021-09-17 | 2023-03-23 | ATAI Life Sciences AG | Preparation of optically active enantiomers of piperonyl amines by resolution of the diastereomeric salts |
| WO2023056472A1 (en) | 2021-09-30 | 2023-04-06 | ATAI Life Sciences AG | Enantiomeric ratios of 3,4-methylenedioxymethamphetamine and related metabolites and uses thereof |
| US11845736B2 (en) | 2021-10-01 | 2023-12-19 | Empathbio, Inc. | Prodrugs of MDMA, MDA, and derivatives thereof |
| EP4457222A4 (en) | 2021-12-28 | 2025-12-24 | Empathbio Inc | Nitrogen oxide-releasing prodrugs of MDA and MDMA |
-
2022
- 2022-09-01 EP EP22865560.1A patent/EP4396305A4/en active Pending
- 2022-09-01 MX MX2024002291A patent/MX2024002291A/en unknown
- 2022-09-01 WO PCT/US2022/042353 patent/WO2023034510A1/en not_active Ceased
- 2022-09-01 US US17/901,504 patent/US11993577B2/en active Active
- 2022-09-01 CA CA3230380A patent/CA3230380A1/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| DUNLAP LEE E. ET AL: "Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine", ACS CHEMICAL NEUROSCIENCE, vol. 9, no. 10, 17 October 2018 (2018-10-17), US, pages 2408 - 2427, XP093029160, ISSN: 1948-7193, DOI: 10.1021/acschemneuro.8b00155 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20230096116A1 (en) | 2023-03-30 |
| CA3230380A1 (en) | 2023-03-09 |
| EP4396305A1 (en) | 2024-07-10 |
| MX2024002291A (en) | 2024-06-28 |
| WO2023034510A1 (en) | 2023-03-09 |
| US11993577B2 (en) | 2024-05-28 |
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Legal Events
| Date | Code | Title | Description |
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| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
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| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
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| 17P | Request for examination filed |
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| AK | Designated contracting states |
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| DAV | Request for validation of the european patent (deleted) | ||
| DAX | Request for extension of the european patent (deleted) | ||
| REG | Reference to a national code |
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| A4 | Supplementary search report drawn up and despatched |
Effective date: 20250728 |
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| RIC1 | Information provided on ipc code assigned before grant |
Ipc: C07D 317/58 20060101AFI20250722BHEP |
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| GRAP | Despatch of communication of intention to grant a patent |
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